The Best Hotels in Countryside, Kissimmee - 2026 Updated Prices

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Our top choices for Countryside hotels

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

1. Drury Plaza Hotel Orlando - Disney Springs Area

21.9 km from Countryside

Brianne

฿6,066 total

includes taxes & fees

14 Oct - 15 Oct

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

2. Embassy Suites by Hilton Orlando Lake Buena Vista South

16.7 km from Countryside

Cassandra

฿3,429 total

includes taxes & fees

18 Oct - 19 Oct

An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

3. Home2 Suites by Hilton Orlando at Flamingo Crossings

26.5 km from Countryside

Roderic

฿3,973 total

includes taxes & fees

19 Oct - 20 Oct

A large hotel with multiple floors, a central courtyard, and a reflective water feature.

4. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

26.5 km from Countryside

Elizabeth

฿4,158 total

includes taxes & fees

26 Oct - 27 Oct

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

5. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

26.6 km from Countryside

Deidra

฿3,343 total

includes taxes & fees

27 Oct - 28 Oct

6. Hyatt Regency Grand Cypress

22.7 km from Countryside

Coleen

฿7,977 total

includes taxes & fees

28 Oct - 29 Oct

A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

7. Kompose Boutique Resort at Theme Parks

20.5 km from Countryside

RAJA

฿3,153 total

includes taxes & fees

30 Sept - 1 Oct

An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.

8. Wyndham Grand Orlando Resort Bonnet Creek

20.3 km from Countryside

Carlos

฿6,275 total

includes taxes & fees

29 Oct - 30 Oct

A hotel with a central entrance, palm trees, and a clear sky.

9. Comfort Suites Maingate East

16.7 km from Countryside

Tiki

฿2,698 total

includes taxes & fees

19 Oct - 20 Oct

A hotel with a large pool, palm trees, and a waterfall feature.

10. Caribe Royale Orlando, WorldHotels Elite

19.4 km from Countryside

Brittany

฿8,526 total

includes taxes & fees

4 Oct - 5 Oct

An aerial view of a resort with a winding pool, sun loungers, and palm trees.

11. Hilton Orlando Buena Vista Palace - Disney Springs® Area

21.8 km from Countryside

Stephanie

฿8,213 total

includes taxes & fees

5 Oct - 6 Oct

A pool area with multiple pools, lounge chairs, and a dining setup.

12. Hilton Orlando Lake Buena Vista - Disney Springs® Area

21.3 km from Countryside

Amy

฿7,380 total

includes taxes & fees

1 Oct - 2 Oct

A hotel room with a sofa, a desk with a TV, a bed, and a view of a building with balconies.

13. Holiday Inn & Suites Orlando SW - Celebration Area by IHG

17.2 km from Countryside

Shamyr

฿2,723 total

includes taxes & fees

1 Oct - 2 Oct

A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

14. Vacation Village Orlando, Celebration

18 km from Countryside

Wilbert

฿3,590 total

includes taxes & fees

29 Oct - 30 Oct

A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

15. Seasons Florida Resort

15.3 km from Countryside

Antonio

฿1,602 total

includes taxes & fees

5 Oct - 6 Oct

A modern waiting area with two black chairs, a small table with a plant, and a large window offering a view of trees and buildings.

16. Travelodge by Wyndham Orlando Lake Buena Vista South

16.7 km from Countryside

Paola

฿2,101 total

includes taxes & fees

12 Oct - 13 Oct

A pool with a waterfall feature, lounge areas, and a building with a green roof in the background.

17. Hilton Vacation Club Mystic Dunes Orlando

19.2 km from Countryside

Juan

฿4,411 total

includes taxes & fees

7 Oct - 8 Oct

A kitchen with wooden cabinets, a microwave, a refrigerator, and two bar stools.

18. Club Sevilla

14.4 km from Countryside

Adanise

฿1,977 total

includes taxes & fees

30 Sept - 1 Oct

A hotel pool area with a modern sculpture, sun loungers, umbrellas, and a large building in the background.

19. Hyatt Place Orlando/Lake Buena Vista

22.6 km from Countryside

Natalie

฿3,175 total

includes taxes & fees

6 Oct - 7 Oct

A breakfast area with a counter displaying hard-boiled eggs, fruits, and muffins. There are two stools and a sign reading "TOP IT BREAKFAST".

20. Tru By Hilton Orlando Convention Center Area, FL

26 km from Countryside

Dia

฿3,181 total

includes taxes & fees

5 Oct - 6 Oct

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Where to stay in Countryside

Find the best Countryside areas for the activities you enjoy most.

A golf course with bunkers, water hazards, and a large lake.

Reunion

The top golf courses and fun-filled water parks are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

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An aerial view of a residential area with numerous houses, roads, and several lakes.

Windsor Hills

While there might not be top attractions in Windsor Hills, you can explore the larger area and discover places like Mystic Dunes Golf Club and Island H2O Live!.

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A sunset over a marshy landscape with a wooden pier extending into the water.

Orange Lake

If you're spending some time in Orange Lake, Walt Disney World® Resort and Orange Lake Golf are top sights worth seeing.

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A lakeside town with a prominent white building, lush greenery, and a distant city skyline.

Lake Berkley

While Lake Berkley may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Medieval Times and Give Kids the World Village.

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Bellavida

Bellavida might not have many top sights, but Medieval Times and Give Kids the World Village are two attractions nearby that you can check out.

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Top Countryside Hotel Reviews

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent

"Staff was friendly. Easy check in and out. Great breakfast."

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"The room was clean and spacious, I love the staff so friendly and helpful and the breakfast and kick back are a great feature of staying there. I love the pool and outside bar area. The fact that you can walk to Disney Springs is a real bonus. No resort fee is definitely a plus."

Walt Disney World Swan

8/10 Good

"The property, grounds and being close to the WDW parks was why we chose the Swan. We were disappointed that Housekeeping was not consistent in keeping our room clean on a daily basis without a call to the front desk. Staff was helpful when we called and made sure we had what we needed if our room was overlooked."

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent

"Came here to say this hotel was great for my wife and I. The amenities were great. 8 minute drive to magic kingdom. The buffet breakfast was phenomenal! Mini Mickey Mouse head waffles were very good! I will definitely be coming back to this hotel !"

Frequently asked questions

What's it like in Countryside?

You'll be sure to have fun exploring Kissimmee's Countryside neighbourhood.

If I need to cancel my hotel reservation in Countryside, will I receive a refund?

Yes, the majority of hotel room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of booking. Enter dates in and click on "Search", then you can filter by "fully refundable" to get top deals in Countryside.

What is there to do in this Kissimmee neighbourhood?

Popular attractions in the larger Kissimmee area include Walt Disney World® Resort, Disney's Animal Kingdom® Theme Park and Old Town. While you're out sightseeing, Silver Spurs Arena and Osceola Heritage Park are a couple of sights to visit in the city.

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Our top choices for Countryside hotels

1. Drury Plaza Hotel Orlando - Disney Springs Area

2. Embassy Suites by Hilton Orlando Lake Buena Vista South

3. Home2 Suites by Hilton Orlando at Flamingo Crossings

4. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

5. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

6. Hyatt Regency Grand Cypress

7. Kompose Boutique Resort at Theme Parks

8. Wyndham Grand Orlando Resort Bonnet Creek

9. Comfort Suites Maingate East

10. Caribe Royale Orlando, WorldHotels Elite

11. Hilton Orlando Buena Vista Palace - Disney Springs® Area

12. Hilton Orlando Lake Buena Vista - Disney Springs® Area

13. Holiday Inn & Suites Orlando SW - Celebration Area by IHG

14. Vacation Village Orlando, Celebration

15. Seasons Florida Resort

16. Travelodge by Wyndham Orlando Lake Buena Vista South

17. Hilton Vacation Club Mystic Dunes Orlando

18. Club Sevilla

19. Hyatt Place Orlando/Lake Buena Vista

20. Tru By Hilton Orlando Convention Center Area, FL

Where to stay in Countryside

Reunion

Windsor Hills

Orange Lake

Lake Berkley

Bellavida

Top Countryside Hotel Reviews

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Frequently asked questions

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